Process for preparing butanone derivatives

Abstract

PCT No. PCT/FR96/00045 Sec. 371 Date Jul. 14, 1997 Sec. 102(e) Date Jul. 14, 1997 PCT Filed Jan. 11, 1996 PCT Pub. No. WO96/21739 PCT Pub. Date Jul. 18, 1996A process for the preparation of a saturated butanone having a terminal substituted aryl group (I) by the selective reduction of an aryl-substituted alpha , beta -unsaturated butanone (II) is presented. The aryl moiety can be mono- or polysubstituted by one or more C1-C6 alkoxy, methylenedioxy or hydroxyl radicals and R is a C1-C6 radical. The alpha , beta -unsaturated butanone (II) is subjected to the action of the enzymes of a yeast or of a filamentous fungus to give a mixture of (I) and an alcohol (III). (I) and (III) are isolated and purified. (III) can be enzymatically oxidized to provide (I).

We claim: 
     
       1. A process for preparing a butanone consisting of the formula (I): ##STR4## wherein Ar is an aryl group that is mono- or polysubstituted by one or more C 1  -C 6  alkoxy, methylenedioxy or hydroxyl radicals and R is a C 1  -C 6  radical, comprising: (a) subjecting a compound of formula (II): ##STR5## wherein Ar and R have the meanings already indicated, to the action of the enzymes of a yeast or of a filamentous fungus to give a mixture of (I) and an alcohol of formula (III): ##STR6## wherein Ar and R have the meanings already indicated; and (b) isolating and purifying said butanone (I).   
     
     
       2. The process of claim 1, wherein said enzymes are produced in situ. 
     
     
       3. The process of claim 1, wherein said enzymes are in the form of a concentrate. 
     
     
       4. The process of claim 3, wherein said concentrate is a protein extract. 
     
     
       5. The process of claim 1, wherein Ar is a substituted phenyl radical. 
     
     
       6. The process according to claim 5, wherein the phenyl radical is substituted by at least one member selected from the group consisting of methoxy, ethoxy, methylenedioxy and hydroxyl. 
     
     
       7. The process according to claim 1, wherein 4-(4-hydroxyphenyl)-butan-2-one is prepared. 
     
     
       8. The process according to claim 1, wherein 4-(4-hydroxy,3-methoxyphenyl)-butan-2-one is prepared. 
     
     
       9. A process for preparing a butanone consisting of the formula (I): ##STR7## wherein Ar is an aryl group that is mono- or polysubstituted by one or more C 1  -C 6  alkoxy, methylenedioxy or hydroxyl radicals and R is a C 1  -C 6  radical, comprising: (a) subjecting a compound of formula (II): ##STR8## wherein Ar and R have the meanings already indicated, to the action of the enzymes of a yeast or of a filamentous fungus to give a mixture of (I) and an alcohol of formula (III): ##STR9## wherein Ar and R have the meanings already indicated; (b) isolating and purifying said butanol (III);   (c) enzymatically oxidizing said purified alcohol (III) to the corresponding butanone of formula (I); and   (d) isolating and purifying said butanone.   
     
     
       10. The process of claim 9, wherein said enzymes of step (a) are produced in situ. 
     
     
       11. The process according to claim 10 wherein Ar represents a substituted phenyl radical. 
     
     
       12. The process according to claim 11 wherein the phenyl radical is substituted by at least one member selected from the group consisting of methoxy, ethoxy, methylenedioxy and hydroxyl. 
     
     
       13. The process according to claim 10 wherein the compound prepared is selected from the group consisting of 4-(4-hydroxyphenyl)-butan-2-one and 4-(4-hydroxy, 3-methoxyphenyl)-butan-2-one. 
     
     
       14. The process of claim 9, wherein said enzymes of step (a) are in the form of a concentrate. 
     
     
       15. The process of claim 14, wherein said concentrate is a protein extract. 
     
     
       16. The process according to claim 14 wherein the compound prepared is selected from the group consisting of 4-(4-hydroxyphenyl)-butan-2-one and 4-(4-hydroxy,3-methoxyphenyl)-butan-2-one. 
     
     
       17. The process according to claim 14 wherein Ar represents a substituted phenyl radical. 
     
     
       18. The process according to claim 17 wherein the phenyl radical is substituted by at least one member selected from the group consisting of methoxy, ethoxy, methylenedioxy and hydroxyl. 
     
     
       19. The process of claim 9, wherein Ar is a substituted phenyl radical.